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Chirality A series of chiral and achiral objects, the interaction of polarized light with organic molecules, the assignment of R- and S- configuration, Fisher projections, and a stereospecific reaction are demonstrated.
Percy Julian, Robert Robinson, and the Identity of EseretholeAddison Ault The Nova production Percy JulianForgotten Genius, which included the very public disagreement over the identity of "eserethole," the key intermediate for the synthesis of the alkaloid physostigmine, left three important chemical questions unanswered. Ault, Addison. J. Chem. Educ.2008, 85, 1524.
Constitutional Isomers |
Enantiomers |
Natural Products |
Stereochemistry |
Synthesis
Evaluating Mechanisms of Dihydroxylation by Thin-Layer ChromatographyBenjamin T. Burlingham and Joseph C. Rettig Presents a microscale experiment in which cyclohexene is dihydroxylated under three sets of conditions and the products determined through thin-layer chromatography. Teams of students evaluate proposed mechanisms for each dihydroxylation in light of the data collected. Burlingham, Benjamin T.; Rettig, Joseph C. J. Chem. Educ.2008, 85, 959.
Addition Reactions |
Alkenes |
Diastereomers |
Mechanisms of Reactions |
Microscale Lab |
Stereochemistry |
Synthesis |
Thin Layer Chromatography
Rapid and Stereoselective Conversion of a trans-Cinnamic Acid to a β-BromostyreneThomas A. Evans The stereoselective synthesis of an aryl vinyl bromide is accomplished in a rapid microscale reaction of trans-4-methoxycinnamic acid with N-bromosuccinimide in dichloromethane. This guided-inquiry experiment links reactivity, stereochemistry, and mechanism in electrophilic addition reactions of alkenes and in E1 and E2 elimination reactions that form alkenes. Evans, Thomas A. J. Chem. Educ.2006, 83, 1062.
Stereochemistry TutorialNicola Burrmann Master the concepts organic stereochemistry with this interactive tutorial. It includes definitions, different three dimensional representations, assigning priorities to stereocenters, and determining the stereochemical relationship between molecules. Each section is followed by a question set that tests knowledge and understanding.
Stereochemistry |
Chirality / Optical Activity
Mage; A Tool for Developing Interactive Instructional GraphicsStephen F. Pavkovic Mage is a graphics program especially well suited for visualizing three-dimensional structures of proteins and other macromolecules. It is an important tool for biochemists and finds many applications in biochemistry courses. We utilize Mage to create interactive instructional graphics of potential use in a wider range of undergraduate chemistry courses, and present some of those applications here.
